| Identification | Back Directory | [Name]
Cis(+/-)-2-hydroxy-N-(2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)benzaMide | [CAS]
287194-38-1 | [Synonyms]
rel-DHMEQ
DHMEQ (racemate)
TRANS-2-HYDROXY-N-(2-HYDROXY-5-OXO-7-OXABICYCLO[4.1.0]HEPT-3-EN-3-YL)BENZAMIDE
2-hydroxy-N-[(1S,6R)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzamide
Cis(+/-)-2-hydroxy-N-(2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)benzaMide
Benzamide, 2-hydroxy-N-[(1R,2R,6R)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-, rel- | [Molecular Formula]
C13H11NO5 | [MDL Number]
MFCD12965045 | [MOL File]
287194-38-1.mol | [Molecular Weight]
261.23 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at -20°C | [solubility ]
DMSO : ≥ 32 mg/mL (122.50 mM) | [form ]
powder | [color ]
white to beige | [InChI]
1S/C13H11NO5/c15-8-4-2-1-3-6(8)13(18)14-7-5-9(16)11-12(19-11)10(7)17/h1-5,10-12,15,17H,(H,14,18)/t10-,11+,12-/m0/s1 | [InChIKey]
IUOMATKBBPCLFR-TUAOUCFPSA-N | [SMILES]
O[C@@H]1[C@@]2([H])[C@](C(C=C1NC(C3=C(C=CC=C3)O)=O)=O)([H])O2 |
| Hazard Information | Back Directory | [Uses]
DHMEQ racemate is a NF-κB inhibitor. DHMEQ racemate is less active than (-)-DHMEQ. | [Biological Activity]
Potentselectiveand irreversible inhibitor of NF-KB th at covalently binds to a cysteine residue.
DHMEQ is a potentselectiveand irreversible inhibitor of NF-KB th at covalently binds to a cysteine residue. It inhibits inflammatory cytokine expression in mice models. DHMEQ is a potent and non/low toxic in vivo anti-inflammatory agent effective in number of animal models. | [in vivo]
The antiarthritic effects of (-)-DHMEQ (DHM2EQ) and DHMEQ racemate (DHM3EQ) are examined on type-II collagen-induced arthritis in DBA1/J mice. This animal model is widely used for evaluation of antirheumatic drugs because of its pathological similarities to human rheumatoid arthritis. The arthritis is elicited and scored. (-)-DHMEQ markedly inhibits type-II-collagen-induced arthritis in mice, whereas DHMEQ racemate tends to only slightly inhibit it[1]. | [IC 50]
NF-κB | [References]
[1] Matsumoto N, et al. Synthesis of NF-kappaB activation inhibitors derived from epoxyquinomicin C. Bioorg Med Chem Lett. 2000 May 1;10(9):865-9. DOI:10.1016/s0960-894x(00)00114-1 |
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